An Overview of Whitey’s Murders: The First Three Groups (3 of 5)

(1) whiteyThe “peace” gave Whitey what he needed a way out of Southie; a way to keep his hand in Southie; time and protection. He’d start hanging around in Somerville with the guys at Marshall Motors (the Hill) because Southie was still too hot. He knew the Mullens did not particularly like him so he kept his distance. He dealt mostly with Pat Nee who was born in Ireland, raised in South Boston, fought in Vietnam, and was one of the Mullen leaders.

In Somerville he was a minor player. The Winters gang of Jimmy Sims and Joe McDonald didn’t particularly like him but they tolerated him because he made no trouble and they respected him because he had done time in the Big House. They thought he talked a little too much but Howie was able to keep the peace. The Roxbury guys, at this time the Martorano brothers  with George Kaufman, had their own businesses to attend to in Roxbury, Dorchester and Quincy so they tolerated him because Whitey was an earner bringing in more money than he was taking out.

Things were quiet after Whitey first joined back in 1972 and he fell in line under the leaders of the two disparate desperado groups on the Hill, John Martorno from Roxbury, Howie Winter from Somerville, both hardened and capable criminals who unlike Whitey had murdered others. The group controlled the gaming and other rackets outside of the Mafia controlled areas and they coordinated their work with the Mafia. There was plenty of business for all to enjoy.

The gang war of the Sixties had brought too much heat and hindered profits. In part, it was said that was why Gerry Angiulo gave Joe Russo the OK to make peace in Southie with Howie Winter. Both sides knew a war would serve no one’s purpose since each side had capable killers; and, although killer for killer the Hill might have had the most brutal guys, the Mafia was always capable of calling in the cavalry from other families.

As 1973, the year the draft would be abolished, rolled in Whitey still is not known or alleged to have murdered anyone.  He is 44 years old. The others would have given Murder Inc. a run for its money. Between this time and 1985, a period of 12 years is the time when it is said Whitey was most active in his killings.

The murders attributed to him can be divided into groups.  The first group of four murders is the Contract Group which were done pursuant to a contract given out by Gerry Angiulo to Howie Winter and John Martorano. Al “Indian Al” Notarangelli had been starting up his own gaming business by intruding on that of Angiulo. He murdered one of Gerry Angiulo’s workers so Gerry  turned to the Hill to help him out. They made some financial arrangements. These murders occurred in the 1973 to 1974 time frame: they were of: Michael Milano, Al Plummer, and William O’Brien all who were innocent of any involvement in the dispute; and Indian Al.

The next group of three murders is the Kill or Be Killed Group where three Mullens in South Boston were wiped out because it was believed they presented a threat to Whitey. These occurred in 1974 and 1975 and the victims were Paulie McGonagle, Tommy King, and Buddy Leonard. The latter two were like peas in a pod and hard as nails – if one was taken out you had to make sure to get the other.

Then there were the four murders in the Hill Group between 1973 and 1976. Each of these men were murdered for different reasons: James “Spike” O’Toole because he was a member of the McLaughlin group and had shot up one of the Roxbury guys quite badly and generally disliked; Edward “Eddie” Connors, another wise guy who as they say in the movies “knew too much” some of which could have hurt guys on the Hill; next was James Sousa who got involved in a scam that ended putting Joe McDonald in the jackpot; and finally there was Richard Castucci who was murdered so that the Hill guys could rip off the New York Mafia guys of money which they owed.

The above eleven murders all occurred between 1973 and 1976. In most of them Whitey played a minor role. The men doing the killing of the Contract Group was John Martorano and Howie Winter, the latter even though implicated by Martorano in them has never been charged. Martorano put a gun to the head of two of the Hill Group, Sousa and Castucci as well as one of the Kill-or be- Killed Group, Tommy King.

In perhaps three of the murders, two of who were rivals to Whitey you would think he would have taken the  lead role. That is not necessarily so. With respect to Eddie Connors he murdered him along with Stevie Flemmi to gain his creds with the Hill.

Then there were his rivals for power in Southie: Paul McGonagle and Buddy Leonard. Martorano tells us Tommy King shot McGonagle while Whitey was there; as for Buddy Leonard, Martorano tells us the “Whitey and his crew” got him. Strange as it seems no one puts a gun in Whitey’s hand and he is depending on others, even in Southie, to do his dirty work.






  1. Matt
    How do we know that Sims and McDonald didnt care for Whitey Bulger? What illegal activities was Bulger doing that earned him a reputation as an “earner”? Am I correct in concluding that Bulger was a custodian after released from prison and then started hanging out in bars with known gangsters and criminals and let it be known that he was looking for work in organized crime? Who do you suspect he got in good with?

    It fascinates me that Bulger has not killed anyone before the age of 44. Any theories as to what set him in that path at such an old age. Then not only does he start late but then he repeatedly murders for a long stretch. I am not a psychologist but I wonder if his long prison sentence, the specific prisons he went to, and the LSD experiments all came together and set the stage for him being able to murder an individual.

    You mention Howie Winter having killed alongside with Martorano. In none of the readings and research that I have done have I seen anything saying Winter murdered anyone. I always thought it was odd that a guy would be the boss of such dangerous killers and yet its never mentioned that he killed anyone.

    • Jerome:

      I think the situation was such that he was intruding on their life style. I also think that Howie Winter in an interview mentioned they did not like him. Some of the women who associated with them suggested that. I can’t put my fingers on the exact quote but I never pictured Whitey as a cuddly type guy who would fit in with the type of gangsters like MacDonald and Sims who were not known for their temperance and pretty much did things together.

      Whitey took over the Killeen action which included most of South Boston; that was what the Mullens wanted a piece of. It was that money that helped him get the Hill’s protection.

      Whitey murdered because he gpt into group of people who liked to commit murders. As I said he had to prove himself. Martorano testified during the Connolly trial that he and “a guy from Somerville” were the two handling the grease guns in the murders for Angiulo; he testified in Whitey’s trial that the guy from Somerville was Howie Winter.

  2. Matt
    This is an excellent breakdown and really sets the stages for the breakdown of the 19 individual murders Whitey is accused of doing. I cant thank you enough for helping us to sort the truth out in this saga. I am reading Deadly Alliance (Ralph Ranalli) AGAIN and its really a treat to re-read it after reading your blog this past year. With that said have you read the book about Greg Scarpa. Its titled DEAL WITH THE DEVIL. That is on my list because it seems like that situation had just as much, if not more, corruption regarding the TEI program. Mind boggling just how much the FBI gets away with as an agency.

  3. Matt- Enjoyed the way you categorized each murder, that helps alot with the timeline and being able to distinguish who is part of what. Matt you are really helping people with the true facts and timeline of these facts. Thanks again for always being a reliable contact and mentor and allowing all the great input from everyone that takes this seriously.

    • Doubting:

      Thanks. Breaking them out into categories and years seems to diminish Whitey’s importance and bring it down close to reality. As you will see when the series is done that it is utterly amazing he could have been attributed to having so much power.

  4. I see no mention of George Kaufmans body shop on Mass ave. Headquarters of Leo Shwartz where Eddie Connors, Tommy Blue Balou, and many other players would show up daily to pay tribute

    • Lewis:

      True – I have not mentioned them. Maybe you can provide me with some insight into it since my knowledge on it is limited. Was it near the Edison set up? Was it one of those chop shops that I’d drive by heading into the South End? How close was it to Howard Johnson’s? Tell me more about the other guys you mentioned.

      • Across the street from Edison on the right. Quarter mile down from Venition restaurant. 3 minutes from Howard Johnsons.

        • Lewis:

          Thanks. Great description. I can picture it – must have walked or driven past it a hundred times going from Savin Hill to the South End. I knew that the Venetian was a hang out for some of the gangsters; I never would have figured out why until you put these locations in close proximity. It reminds me of the time I was doing a wiretap and bug on Abe Sarkis. He received a call that went like: “Abe this is very important. Meet me at the Venetian as soon as you can.” We could hear Abe say he had to leave. Obviously, if we could connect Abe with that voice we would have put together an important link in organization because the guy was clearly above Abe. Do you think the state police who were doing the tap put surveillance on Abe? If you said no you would be right. They were too interested in trying to jam in a fellow state trooper that they let this pass. To say I was livid when I heard about it the next day is a great understatement.

          • Leo Shwartz was the highest ranking bookmaker loan shark at the time. He would meet with Abe many times at the body shop.